Pseudomonic acid A is a new antimicrobially active compound isolated as the major metabolite of a strain of Pseudomonas fluorescens. Its demonstrated lack of cross resistance with other antibiotics and its mycoplasma activity make it a potential macrolide competitor and useful human respiratory tract agent. A total synthesis of this antibiotic is proposed which relies on the reaction of a stabilized phosphorane with an appropriately functionalized tetrasubstituted tetrahydropyran. Methods for the direct stereoselective epoxidation of homoallylic alcohols will be investigated. The scheme envisaged should permit ready access to a variety of interesting analogue structures.